Literature DB >> 18698823

Synthesis of carbapyochelins via diastereoselective azidation of 5-(ethoxycarbonyl)methylproline derivatives.

Wathsala Liyanage1, Laksiri Weerasinghe, Roland K Strong, Juan R Del Valle.   

Abstract

Two configurationally stable carbon-based analogues of pyochelin have been prepared from Boc-pyroglutamic acid-tert-butyl ester in 11 and 13 steps. Introduction of the amino group was achieved by a highly diastereoselective electrophilic azidation reaction to afford novel bis-alpha-amino acid proline derivatives.

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Year:  2008        PMID： 18698823      PMCID： PMC2802343          DOI： 10.1021/jo801294p

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

1.  A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones We thank Professors Brauman, Stack, Trost, and Wender for many helpful discussions. C.G.E. is the recipient of an NSF Predoctoral Fellowship. J.D.B. gratefully acknowledges the Camille and Henry Dreyfus Foundation for a New Faculty Award. Special thanks are extended to Merck Research Laboratories, Johnson Matthey, Professor Michael P. Doyle, and Stanford University for generous gifts and financial support.

Authors:  Christine G. Espino; J. Du Bois
Journal:  Angew Chem Int Ed Engl       Date:  2001-02-02       Impact factor: 15.336

2.  Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues.

Authors:  A Zamri; I J Schalk; F Pattus; M A Abdallah
Journal:  Bioorg Med Chem Lett       Date:  2003-03-24       Impact factor: 2.823

3.  A silver-catalyzed intramolecular amidation of saturated C--h bonds.

Authors:  Yong Cui; Chuan He
Journal:  Angew Chem Int Ed Engl       Date:  2004-08-13       Impact factor: 15.336

Review 4.  Iron acquisition and its control in Pseudomonas aeruginosa: many roads lead to Rome.

Authors:  Keith Poole; Geoffery A McKay
Journal:  Front Biosci       Date:  2003-05-01

5.  Isolation of an iron-binding compound from Pseudomonas aeruginosa.

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Journal:  J Bacteriol       Date:  1979-01       Impact factor: 3.490

6.  An iron delivery pathway mediated by a lipocalin.

Authors:  Jun Yang; David Goetz; Jau Yi Li; Wenge Wang; Kiyoshi Mori; Daria Setlik; Tonggong Du; Hediye Erdjument-Bromage; Paul Tempst; Roland Strong; Jonathan Barasch
Journal:  Mol Cell       Date:  2002-11       Impact factor: 17.970

7.  Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin.

Authors:  May Xiao-Wu Jiang; Bohan Jin; Jennifer L Gage; Alain Priour; Gordon Savela; Marvin J Miller
Journal:  J Org Chem       Date:  2006-05-26       Impact factor: 4.354

8.  Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition.

Authors:  Leonardo Manzoni; Daniela Arosio; Laura Belvisi; Antonio Bracci; Matteo Colombo; Donatella Invernizzi; Carlo Scolastico
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

9.  Siderocalin (Lcn 2) also binds carboxymycobactins, potentially defending against mycobacterial infections through iron sequestration.

Authors:  Margaret A Holmes; Wendy Paulsene; Xu Jide; Colin Ratledge; Roland K Strong
Journal:  Structure       Date:  2005-01       Impact factor: 5.006

10.  Mutasynthesis of siderophore analogues by Pseudomonas aeruginosa.

Authors:  R G Ankenbauer; A L Staley; K L Rinehart; C D Cox
Journal:  Proc Natl Acad Sci U S A       Date:  1991-03-01       Impact factor: 11.205
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  1 in total

1.  Synthesis and conformational analysis of bicyclic extended dipeptide surrogates.

Authors:  Sujeewa Ranatunga; Wathsala Liyanage; Juan R Del Valle
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354
  1 in total

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